Things To Do In Annapolis At Night

Annapolis, Maryland is a charming city that comes alive at night. Enjoy Annapolis’ stunning waterfront with all the yachts, sailboats, and river-goers as you wander down Main Street for a food crawl.

Things to do in Annapolis at night include visiting historic sites, taking a boat tour, dining at waterfront restaurants, and enjoying live music and entertainment.

Strolling along the town allows couples and friends to take in all the beautiful stores and restaurants with delicious seafood options or succulent barbecue joints.

At night, the Annapolitan skyline is illuminated by lights from local buildings, creating a scenic setting perfect for long conversations about life or late-night strolls for stargazing.

Overview of Annapolis

Annapolis, Maryland is a vibrant city with a rich history and culture. Historians have documented the earliest settlers living in Annapolis as early as 1649 and while much has changed since then, one thing remains: Annapolis is a unique place full of exciting opportunities.

Despite its small size, it is home to the United States Naval Academy, giving the city an international flair and many tourist attractions, including Historic Downtown Annapolis, which still has many colonial buildings standing.

Tourists flock to Annapolis for its waterfront beauty, cobblestone streets, and famous inns or to see the State House which served as America’s first Capitol when George Washington resigned his commission in 1783.

As if that weren’t enough, visitors can explore local markets where vendors sell vintage jewelry, clothing, pottery, and antiques; go shopping at crowded malls, or take free walking tours of the area.

Whether you are looking for a quiet getaway weekend or a bustling atmosphere full of activities and cultural attractions for your vacation plans, you need to look no further than Annapolis!

Unique Nightlife in Annapolis

When you think of nightlife, Annapolis is far from the first place that comes to mind. But this picturesque coastal city on the Chesapeake Bay has plenty of unique things to do at night and all within walking distance of the historic downtown!

Whether you’re visiting for a weekend or an extended vacation, there’s sure to be something special to experience in Annapolis.

From award-winning restaurants and organically flavored shaved ice shops to authentic theater productions and off-the-beaten path pubs, the nightlife in Annapolis offers something for everyone.

Explore live music, craft breweries, wineries, sports bars, theatre or an outdoor movie night near one of its many park settings.

Enjoy drinks and casual fare with a fantastic water view on an outdoor patio overlooking bustling downtown harbor activity.

You can visit some of the small independent coffee shops where local students like to hang out late into the evening discussing current events and artsy philosophies in their own language. This charming capital city will surprise you with how much fun awaits you after sundown.

Places to Explore During the Day

Annapolis offers a vast array of activities and places to explore during the daytime. From its vibrant waterfront, with delicious seafood and all kinds of boats, to leisurely walking tours that take you through centuries-old architecture.

From historic sites such as the State House or the United States Naval Academy to shopping centers for all your needs.

For those looking to explore the outdoors, there are plenty of options. Visit Sandy Point State Park for a hike or take a kayak around Annapolis Harbor and experience the beauty of Chesapeake Bay while spotting some local wildlife.

Check out one of its many farmer’s markets where you can find fresh produce and local specialties, grab a bite to eat along Main Street, or spend the day in one of its many parks and green spaces. With so much to explore, Annapolis is a great place to spend the day, no matter what your interests are!

US Naval Academy Museum

As the nation’s oldest military academy, the US Naval Academy Museum offers visitors a unique opportunity to explore some of the Academy’s most important and historical artifacts and documents.

From entrance documents signed by President George Washington to uniforms worn by famous officers and priceless artworks, this museum is filled with fascinating memorabilia and personal stories from over two hundred years of military history.

William Paca House & Garden

The William Paca House & Garden in Annapolis, Maryland is a great place to explore the colonial history and culture of the Chesapeake Bay region.

Visiting this National Historic Landmark will bring insight into the lifestyle of esteemed statesman William Paca who, during his lifetime, was governor of Maryland and a signer of the Declaration of Independence.

Built-in 1763, the four-part five-acre estate is now open to visitors who wish to explore the stunningly preserved Georgian-style landscape and rooms filled with 18th-century antiques and furnishings.

Within its walls and grounds are remarkable examples of 18th-century brickwork that were recently uncovered after decades of backyard gardens.

Special tours are available for those interested as well as programs on topics such as gardening and history, making this an educational experience for all ages.

There are seasonal interpretive living history programs like Shopkeeper’s Saturday held throughout the year so everyone can experience life during colonial times. All in all, visiting the William Paca House & Garden is a must while exploring Annapolis!

Maryland State House

The Maryland State House in Annapolis, located near the mouth of the Severn River a quick drive from Washington D.C. is one of the oldest state government buildings in continuous legislative use in the United States.

It was constructed in 1772 and since then has been the home to five different branches of Maryland’s government all located within the same building.

The amazing details and grandeur are still maintained to this day with its cathedral-like interior and massive dome that rises 60 feet high and is covered with 23-karat gold leaf which can be seen at an incredible distance.

A notable attraction within the state house is George Washington’s decorated office where he resigned his commission as Commander in Chief of the Continental Army on December 23rd, 1783 it was recently brought back to its original condition as it appeared during Washington’s time.

Annapolis places a high regard for honoring its history, but also looks towards future endeavors as well; just a few steps away from the state house lies Market House Square which houses many shops and restaurants that bring life to the downtown community today.

Local Restaurants and Bars

Annapolis, Maryland is known for its dazzling harbor and rich colonial history, but many come to experience the thriving restaurant and bar scene.

From upscale eateries to casual waterfront dining, the selection of restaurants that are local to Annapolis is vast and varied.

Things To Do In Annapolis At Night Local Restaurants and Bars

Harry Browne’s

If you’re looking for a great night out in Annapolis, look no further than Harry Browne’s. This unique local landmark offers an unbeatable experience with its cozy Chelsea lounge. A restaurant featuring upscale New American cuisine, and a wide variety of craft cocktails.

Regardless of whether you are looking for an intimate dinner setting or a wild night out, Harry Browne’s will have something to offer.

For a more intimate experience, take advantage of the romantic low-level lighting and a full menu for two perfect for date night.

If you’re in the mood for something more social and energetic, browse their extensive list of signature craft cocktails and live music from local artists.

Galway Bay Irish Pub & Restaurant

Annapolis Galway Bay Irish Pub & Restaurant is an excellent place to get a taste of traditional Irish cuisine. From fish & chips and steak dinners to savory soups and an extensive selection of beers, the menu at this lively pub provides many delicious options for hungry patrons.

In addition, the cozy atmosphere and friendly staff make it the go-to spot for friends looking for a laid-back evening out.

Guests can also enjoy watching sports games on one of the 15 TVs located around the restaurant as well as live music every Thursday and Sunday from local performers.

It’s no wonder why Galway Bay has become such a hit with locals looking for a relaxed night out or just a good meal.

Pusser’s Caribbean Grille

Located in downtown Annapolis, Maryland, Pusser’s Caribbean Grille is a hotspot for locals and visitors alike.

Boasting a spread of New American and Caribbean-inspired dishes, the restaurant gives food lovers an opportunity to experience cuisine from America’s Southern Coast.

From traditional classics like Crack Conch Fritters to adventurous dishes like Jerk-Style Mac & Cheese, Pusser’s coastal cooking is sure to please just about everyone.

In keeping with tradition, the restaurant also serves up tasty island cocktails such as Mai Tais and Painkillers.

Beyond their bold flavors and zesty ingredients, patrons are greeted by the warm hospitality that truly makes them feel at home in the Chesapeake region.

With colorful decor reminiscent of the Caribbean Sea islands and upbeat dock tunes coming through the speakers, Pusser’s Caribbean Grille is second to none when it comes to delivering an authentic Annapolitan dining experience.

Theaters and Arts Venues

Annapolis is a great city for anyone looking for a wonderful night out at the theater or enjoying some art! A visit to Maryland Hall for the Creative Arts is a must-do, no matter the time of day. Attendees can catch amazing plays, concerts, dance performances, films, and even comedy shows.

Annapolis Shakespeare Company is also in town and offers regular outdoor performances in Annapolis’ charming outdoor spaces – making them socially distanced and totally accessible.

The drive-in movie experience is not dead in Annapolis either – with plenty of chances to catch major films courtesy of Annapolis Film Lab or one of the other frequent drive-ins around town.

Art lovers are invited to enjoy artisan exhibitions and music events found at Anne Arundel Community College as well as at Maryland Hall’s galleries. Museums such as the Chesapeake Children’s Museum provide more details about local history and culture.

Whether you are interested in art or just want to get away from your everyday life, there are few cities that offer such an exciting array of activities for all ages as Annapolis does!

Theaters and Arts Venues

Annapolis Opera

Annapolis is an amazing city that provides the best of both worlds: a small-town feel and a charming historic downtown, while also offering plenty of things to do year-round. One of its shining jewels is the Annapolis Opera, which began in 1976 and continues to bring world-class performances to its community.

With a goal to unite artistic excellence with education and innovation, the opera strives to create beautiful productions that touch hearts and spark curious minds.

When it comes to their production schedule, patrons can look forward to seeing works from the Baroque Era all the way through modern-day masterpieces.

If you’d rather not sit through a full performance, workshops and other special events revolving around classical music are also easily accessible.

Maryland Hall for the Creative Arts

The Maryland Hall for the Creative Arts, located in Annapolis, is an impressive facility that serves as a hub for creative expression and arts education throughout the region.

It hosts many community-based and professional productions, as well as classes, camps, workshops, and seminars.

Music enthusiasts can take advantage of the Concert Series on its Haas Innovation Stage, which features local and international performers.

Those interested in visual arts have access to dynamic exhibitions at the galleries of its Rosenberg Gallery or the Walters & Roz Galleries where professional artists showcase their work. Patrons can also purchase works directly from local artisans through their artist vendor shop.

Aside from its mainstay of artistic offerings, it also hosts an inventive array of special events including open mic nights and even an annual summer camp for local children.

Maryland Hall for the Creative Arts’ unique atmosphere encourages creativity and collaboration among a diverse range of art lovers making it a one-of-a-kind attraction in Annapolis.

Rams Head On Stage

Rams Head On Stage in Annapolis, MD is a premier music venue that has been hosting top-level live music acts for over 30 years.

Located in downtown Annapolis, the theater offers an intimate setting ideal for enjoying plenty of genres, ranging from jazz to blues, folk to alternative rock, classics to country, and everything in between.

The space has welcomed hundreds of legendary artists such as Fleetwood Mac, George Thorogood, Gillian Welch, and Cheap Trick.

Its unique purpose-built concert hall allows fans and performers alike to experience top-quality sound from every vantage point in the room.

In addition, to live shows, the venue encourages patrons to visit its lobby bar for drinks and snacks before or during a show. Beer selections by local Maryland breweries make this establishment stand out among other area venues.

Whether you are already an avid fan of Rams Head On Stage or looking forward to your first no-hassle night out filled with great music and friends, there is something sure to please everyone who visits this historic venue.

Shopping Spots

When visiting Annapolis at night, one of the best things to do is explore the eclectic shopping spots. Shops range from high-end boutiques where you can find luxurious clothing and accessories, to unique thrift stores boasting vintage and obscure items.

Everyone in your party is sure to find something they love  so long as they keep a flexible budget!

Along with great boutique shops where you’ll find one-of-a-kind finds, there are also great places for souvenirs.

Arm yourself with grand knowledge from knowledgeable local shopkeepers who can tell you about hidden gems throughout town.

A cozy evening stroll through the city streets will give you the opportunity to find wonderful pieces that you don’t necessarily see elsewhere.

Whether exploring for something special or just some fun window shopping – Annapolis is full of unexpected surprises that make for an enjoyable night out on the town!

Shopping Spots

Annapolis Towne Centre at Parole

Annapolis Towne Centre at Parole offers something for everyone. Located in Annapolis, Maryland, it is a shopping and entertainment hub with more than 100 specialty stores, excellent dining options to satisfy all tastes, and plenty of activities for both adults and children alike.

Visitors can browse stores like Apple, Saks Fifth Avenue OFF 5TH, H&M, Sephora, Dick’s Sporting Goods, Target, and much more before stopping in one of the many restaurants.

Afterward, they can enjoy a movie at the onsite Regal cinema or take a restorative walk through the outdoor park. For those looking to experience more of the city’s historic charm, there are two Baltimore Water Taxi stops where visitors can explore downtown Annapolis or travel over to Eastport for a delicious meal.

Whether you’re shopping for essentials or seeking out some fun activities indoors or outdoors Annapolis Towne Centre has plenty of options to make any visit complete.

Westfield Annapolis Mall

Westfield Annapolis Mall is a shopping, dining, and entertainment destination located in Maryland’s capital city. With over 100 stores including Macy’s, JC Penney, L.L.Bean, Sephora, and Nordstrom Rack shoppers are sure to find something special.

Foodies will enjoy several restaurants ranging from quick eating choices such as Au Bon Pain to delicious sit-down spots like Fleming’s Steakhouse and Famous Dave’s BBQ Pit.

The mall also offers an innovative event space where shoppers can come and enjoy everything from live music performances to holiday parties for the whole family.

With hand-crafted cocktails available at DFW Express Beer & Wine Garden, a 12-screen AMC Theater for moviegoers, and kid-friendly spaces like the La Petite Playdate Area, Westfield Annapolis Mall has unique offerings that can’t be found elsewhere in the area.

Maryland Avenue & State Circle Area

The Maryland Avenue and State Circle area of Annapolis is the perfect place to spend an evening out in the town. With a variety of restaurants, pubs, bars, and galleries, you can find something to do no matter what your style is.

There’s a local craft brewery nearby that makes some of the best beer in town. Dining options range from hearty bar food to refined fine dining so whatever your preference, there’s something for everyone to enjoy.

When you’re done with dinner, catch a show at Rams Head Live or explore the nearby galleries of Maryland Avenue and walk away with artwork representing the true spirit of Annapolis.

No night in Annapolis is complete without some romantic strolling around State Circle – enjoying the freshly lit flowers before settling in at one of the many cocktail lounges and bars close by, it’s definitely a great way to end your night.

Outdoor Activities

Annapolis is a fantastic destination to explore and the outdoor activities offered in the city are nothing short of amazing. From exploring historic sites like the William Brown House, built in 1770, to kayaking on Spa Creek, Annapolis offers an abundance of outdoor recreation for people to enjoy.

Cyclists love riding through Annapolis’ beautiful streets and trails located throughout Quiet Waters Park, while hikers can enjoy navigating any number of trails that feature stunning wildlife and waterfront views.

You can spend a day fishing at Thomas Point or stroll along one of Analpolis’ lush gardens filled with vibrant wildflowers or sample some delicious seafood from the markets.

With so much to do outdoors, there is something for everyone in Annapolis visitors are sure to be captivated by its beauty and history.

Parks and Outdoor Activities

Sandy Point State Park

If you’re looking for a fun and memorable way to spend your evening in Annapolis, look no further than Sandy Point State Park.

Located on the Chesapeake Bay and nestled into the western shore of Maryland, this 241-acre park is the perfect spot for outdoor activities like fishing, swimming, boating, camping, and hiking. On summer nights, be sure to get there in time to witness an incredible sunset over the water.

Afterward, wander along one of the trails that run along the shore and take in spectacular views of the marshes and serene coves.

If you’re feeling really adventurous, pitch a tent at one of the many campsites tucked away in heavily wooded areas throughout the park.

No matter how you decide to spend your night here, it’s sure to be a magical experience that will leave you with lasting memories.

Quiet Waters Park

Annapolis is a beautiful city with picturesque views and plenty of activities that are perfect for entertaining yourself during the night. One such activity is Quiet Waters Park, located on the shores of the South River. This park boasts a variety of features designed to make each visit special.

The park offers an ice skating rink and a carousel, which is great fun for both adults and children alike. There’s also an amphitheater, where visitors can enjoy music or theatrical entertainment during the evening hours.

Boating and fishing are two other favorite pastimes here; take out a canoe or kayak for some peaceful paddling or rent a motorboat for more thrilling water adventures.

Finally, make sure to check out the trails throughout the park, which provide scenic backdrops as you travel from one activity to another.

No matter how you spend your time in Quiet Waters Park at night, it’s certain to be memorable and enjoyable!

Annapolis Harbor

Annapolis Harbor is a picturesque and historic part of the landscape of Annapolis, Maryland. Looking out onto the Chesapeake Bay, it’s an ideal place to relax and take in the beauty of nature.

Part of the harbor is dedicated to recreational activities like boat docks, paddle boarding, and kayaking, while other parts offer stunning views of the famous Naval Academy on rocky cliffs or sunsets above historic buildings.

Considered a destination for both visitors and locals alike who come to experience its unique culture and maritime heritage; there’s plenty to explore in this vibrant cityscape.

A stroll through the harbor reveals stories from its lengthy past and present-day places to enjoy seafood catches of fishermen along with cozy restaurants offering breezy outdoor patios that line its waterfront boardwalks.

Offering a stunning spectacle all year round for those who take the time discover its hidden gems, Annapolis Harbor embodies why Annapolis is the finest regional destination for sightseeing by land and by sea.


In conclusion, there’s no shortage of things to do in Annapolis at night. From the live music venues and the exciting nightlife to great dining experiences and unique shops to explore, the city makes for a great backdrop to an unforgettable evening.

For those who prefer outdoor activities, there are plenty of choices too whether it is stargazing at night on the banks of Spa Creek or touring quietly around the Chesapeake Bay by boat.

With something for everyone, nighttime in Annapolis is sure to be filled with thrills and memories that will last a lifetime.